Kelly's Diary 177 - Cockteaser
Copyright© 2025 by Kelly85
Chapter 5: Doing Tony in His Sleep
Erotica Sex Story: Chapter 5: Doing Tony in His Sleep - Flirt, lush, tramp, slut, cockteaser, bitch, even whore... I've been called them all. I guess it comes with the territory when you love sex and live by a "if you got it, flaunt it" attitude. I'm not afraid to admit I LOVE to tease. It's fun to see what a man will do using nothing more than the offer of your body for incentive. People ask me if I've ever NOT gotten what I wanted from a guy, at least sexually speaking. Well, my best friend's brother was one of my greatest challenges.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Ma/ft Fa/Fa Consensual True Story Masturbation Oral Sex
We finally got up and got our nighties on. As we dressed, I noticed the door was open - not much but just a crack. Maybe it had just opened that much on its own; or maybe it had received a little help along the way. Had someone watched us? Would I ever know for sure? In any case, I opened the door before Beth noticed it hadn’t been shut tightly. Stepping out into the dark hallway, I reached for a light switch and turned on the overhead hall lights, one at each end of the hall.
Tony’s door was next to Beth’s and was closed tightly. Was he inside? Was he masturbating, hopefully about seeing me and his sister playing together? The bathroom was directly across from his door so I walked down and just as I was about to enter, his door opened and he stepped out in a hurry, knocking me over in the process, on his way to the bathroom.
“Sorry,” he apologized quickly, reaching down to help me up.
Of course, my nightie had pulled up in the process and needless to say, I wasn’t wearing anything underneath so he had his first (maybe second?) view of my pussy. The shoulder straps had also mysteriously fallen to my elbows, letting the top slide down and my boobs spilled out. For all intents and purposes I was naked as my nightie was now bunched up around my waist. As he helped me up, Tony was staring at my nudity. Of course, I wasn’t exactly hurrying the process along either as I reveled in the looks he was giving me. I guess catching him by surprise like this put him off balance and he wasn’t thinking about what he was doing, letting his instincts take over instead.
“Tony! Shit! What the hell are you doing with her?”
Oops, I’d forgotten about Beth and now she was just behind me, the anger in her voice back once again. Tony bolted for the bathroom like a deer being shot at, slamming the door behind him to leave me standing there all alone to face the fury of Beth.
“Hmmmmmm, I suppose your nightie just accidentally all but fell off?” she said, a small smile starting to break through her veneer of seriousness.
“I guess so...” I said, biting my tongue as I tried not to laugh.
“I saw you fall ... an NFL kicker would have been proud of such a nose dive,” she started to tease me. “Damn, be honest with me ... did he even really touch you?”
“Well...” I let it draw out, not really answering her one way or the other but she got the picture.
Beth grabbed me by the hand and practically pulled me back to her room. Once inside, she closed the door and this time I noticed she made sure it was closed tightly. Was she just being overly cautious or had she noticed what I’d done before? If she HAD, then she was certainly being more circumspect about it than I would have expected.
“Well you certainly gave him an eyeful, I have to hand you that” she congratulated me, although her tone didn’t exactly match her words. “Poor guy’s probably jacking off in there right now about it.”
My eyes widened and a smile came to my face. She quickly interpreted my expression and shook her head. “and NO ... you can’t go down and help him.”
We both laughed as she correctly identified my feelings at the moment. As things turned out, I wouldn’t see Tony again before we went to bed but as we masturbated later before falling asleep, you better believe I was dreaming about him jerking off about us. As I came, I would imagine was how much perfectly good cum was being wasted - and what I would like to do with it!
We both fell asleep almost instantly but somewhere in the middle of the night I woke up. I must have been dreaming something pretty special because I was soaking wet between my legs and I had this overwhelming feeling of horniness that was like an uncontrollable itch. God, it was driving me nuts! I had awoke facing towards the outside of the bed, my bare butt pressed up against Beth’s as evidently she had rolled in the opposite direction during the night. The feel of her warm soft ass just made me feel all the worst, or at least all the hornier. I wanted to masturbate as my hand cupped my steaming hot crotch but I knew in the mood I was in there was no way to do it without waking Beth so I got up and decided to go to the bathroom where I could let myself go a little more.
As I quietly slipped off the bed, Beth stirred and for a moment I thought she would wake up. I waited, hoping that maybe she would find herself in a similar situation as me and maybe we could each help the other out but she just moaned a little, more of a meow than a groan. Hmmm, what was she dreaming about? She was showing no signs of consciousness so I grabbed my nightie, pulled it over me and then carefully opened the bedroom door. Peeking out into the darkened hallway, I saw it was empty except for the light coming from one of those greenish luminescent nightlights people plug into the wall outlets. At least I didn’t have to turn on the hallway lights or try to make my way blindly down a dark hall.
Just as I reached the bathroom door, I heard a grunt from across the way and I saw that Tony’s bedroom door was about halfway open. Although he didn’t have a teddy bear nightlight or anything like that, there was more than enough moonlight streaming in through the open curtains that I could clearly make him out on the bed. Damn, he was stark naked! Any thoughts of masturbating alone in the solitude of the bathroom immediately disappeared as I stared at him through the open bedroom door.
Tony was lying on his back, his covers thrown off, unknowingly displaying his handsome nude form to anyone who might walk by. Of course, he probably never expected anyone to walk by in the first place, and even then he most likely had the covers over himself when he fell asleep, at least it appeared so from the way they had been kicked to the side. Damn, I was staring at the nude body of a sexy, hunky nineteen year old guy, the first time I’d ever seen this particular one naked.
OK, so I’m only human. Naturally my eyes went immediately to his midsection where his flaccid cock was laying over limply on a dark bed of thick pubic hair. It was just my bad luck that he wasn’t having a wet dream. I’d love to have seen it all nice and hard, cum dribbling from it as he dreamed of maybe fucking me? If I was horny before, you can only imagine how I was feeling now with this temptation literally laying out in front of me!
The heck with it, my hand slipped between my legs and I started to touch myself as I leaned against the door frame. Every instinct in me was screaming for me to go in his bedroom and do something, anything, whatever I wanted - and I certainly wanted a lot. At the same time, there was still some semblance of sanity remaining inside of me that was warning me as to what a horrible risk I’d be taking. What if Beth woke up, found that I was missing, and decided to see where I’d gone off to? No doubt she would have her suspicions from the start knowing me. Catching me masturbating as I looked at him would have likely drawn a sigh from her and a tug back to her room, but at least she could handle that knowing how little it took to get me started touching myself. Besides, I would only be fantasizing about her brother, not really doing anything. However, catching me in his bedroom, doing who knows what nasty things with him, now THAT would be a totally different story.
Honestly, I wondered if our friendship, as strong as it may be, would even survive such a betrayal of her trust? When I fucked her dad it almost broke us apart but since she had fucked my dad as well, I figured we were even and so we managed to get through it. Now as for fucking her brother ... after all she had stressed with me about NOT doing it, would it be the straw that broke the back of our relationship?
Tony wasn’t stirring, not even a periodic snore or anything. It was as if he was unconscious or in some sort of coma. What would he have done had he known I was staring at him, standing at his doorway almost naked with my finger pushed up inside of my pussy as I imagined it was his dick inside of me, the same dick I was now staring at in the moonlight? Would he be embarrassed or turned on? Of course in my fantasies that I was dreaming at the moment, he would sit up and offer his dick to me, telling me to suck him and then have me climb on top and slip it inside of my tight wet pussy. My finger thrust up into me and I barely managed to stifle a gasp as I felt my orgasm beginning to arise with me. God, my knees felt like they were about to buckle as I stared at his dick, allowing the ebb and flow of my passion to fill me with the most incredible sensations.
God I wanted his dick in me! Oh my god, did I say I wanted his hard dick in me NOW? ` Allow me to blame my orgasm for what happened next. Like, I was feeling so hot, so GOOD, so HORNY, that even the last vestiges of my conscience and worries about Beth simply faded away without another thought. I wasn’t even thinking about her anymore. I wasn’t really thinking about anything for that matter.
My body was running on autopilot, reacting rather than being controlled, letting the most primal instincts take over. I was breathing hard, my hand clamped to my pussy, unwilling to release my hold of it for even a moment as it was like I was some sex puppet on a string, with someone else manipulating me, driving me to do this, forcing me in such I way I couldn’t resist the temptation any longer.
Suddenly I was next to his bed, looking down at the object of my desires. I didn’t even recall walking from the door to his bedside, it was like I’d been in another world for a few moments or someone - or something, had momentarily taken over my consciousness. My hand was still pressing on my pussy, my palm putting pressure on my sensitive clit, keeping me on the verge of another orgasm but not quite there yet. His dick was only inches away now. Yes, it was flaccid and small, but it bore so much promise!
I started to reach out to touch it but halfway there it was like something in me was trying to break out from wherever I’d caged it away. For a brief moment I started to pull back, knowing what I was about to do was wrong but it only lasted a second and then my pussy practically cramped I felt so horny. Really, what difference would it make so long as I didn’t wake him? Who would ever know?
I lightly touched the side of his soft dick with the tips of my fingers, half expecting him to bolt up and scream or who knows what. Well, one thing I was learning about Tony - he was dead to the world when he was asleep. As my trembling fingertips lightly touched him along the length of his dick, he never even twitched - not even his dick. My fingers brushed against his thick pubic hair. It was soft yet had a coarseness like that of a soft hairbrush. I leaned over and I could actually SMELL him, the thick musky odor of a man’s crotch. It was a fragrance I loved and I breathed it in deeply, savoring the heavy aroma of his sex.
Emboldened by his complete lack of response, I gingerly put my hand around his limp dick, not moving at first but rather just allowing it to rest in the palm of my hand with my fingers wrapped gently around it. It was actually a rare experience for me. Mot times by the time I got my hands on a dick, especially a teenager’s, it was either fully erect or well on its way. To feel Tony’s dick in its “natural” state was rather exhilarating.
Just then I thought I heard a noise and my hand pulled away from his dick instinctively. It turned out to be just the wind - I heard it again and realized it was a tree branch against the side of the house, but my sudden movement seemed to have stirred Tony. He made a sort of soft, groaning sound but then that was it and once again he was like in a coma. I held my breath until I felt myself turning blue, afraid to even move lest I awaken him.
Finally I got my courage back and once again I felt his soft cock in my hand. This wasn’t the first time I’d ever fondled a guy’s cock while he was sleeping, not by a long shot. It WAS, however, the first time I’d done it to a guy who didn’t go to sleep with me next to him, or at least in some way wouldn’t have been totally surprised to awaken and find my hand wrapped around his dick.
After a couple of minutes, my hand seemed to gain a mind of its own and I watched, more fascinated than anything else, as my hand began to seemingly start to move as if controlled by some unseen force. I was gently jerking him off, pulling on him ever so gently, just enough to stimulate his dick. Slowly, ever so slowly, I began to feel him react. At first it was hardly noticeable but eventually it was unmistakable - he was becoming erect!
It was one of the things I loved about dicks - they not only had their own head but they seemed to have a mind of their own as well. Men can’t seem to control them while they are awake, so why should it be any different while they are asleep? Cock heads didn’t seem to need sleep though, they reacted no matter what the rest of him was doing!
To read the complete story you need to be logged in:
Log In or
Register for a Free account
(Why register?)
* Allows you 3 stories to read in 24 hours.